Details
| Original language | English |
|---|---|
| Pages (from-to) | 4559-4564 |
| Number of pages | 6 |
| Journal | Journal of Organic Chemistry |
| Volume | 67 |
| Issue number | 13 |
| Early online date | 10 May 2002 |
| Publication status | Published - 1 Jun 2002 |
| Externally published | Yes |
Abstract
α-Galactosyl ceramide has been identified to be a potent stimulatory agent for a novel immunological process, mediated by CD1 molecules. This paper describes a short and efficient synthesis of α-galactosyl ceramide. Starting from commercially available 2-deoxy galactose, a suitable sphingosine derivative was obtained in nine steps and 36% overall yield, which was subsequently glycosylated to give the target molecule. This flexible route will provide various glycolipids for further exploration of this interesting biological process.
ASJC Scopus subject areas
- Chemistry(all)
- Organic Chemistry
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In: Journal of Organic Chemistry, Vol. 67, No. 13, 01.06.2002, p. 4559-4564.
Research output: Contribution to journal › Article › Research › peer review
}
TY - JOUR
T1 - Synthesis of a-Galactosyl Ceramide, a Potent Immunostimulatory Agent
AU - Plettenburg, Oliver
AU - Bodmer-Narkevitch, Vera
AU - Wong, Chi Huey
N1 - Funding Information: O. P. acknowledges a fellowshipof the Deutsche Forschungsgemeinschaft. V. B.-N.acknowledges the Swiss National Chemical Societyfellowship. This research is supported by the Skaggsfunds
PY - 2002/6/1
Y1 - 2002/6/1
N2 - α-Galactosyl ceramide has been identified to be a potent stimulatory agent for a novel immunological process, mediated by CD1 molecules. This paper describes a short and efficient synthesis of α-galactosyl ceramide. Starting from commercially available 2-deoxy galactose, a suitable sphingosine derivative was obtained in nine steps and 36% overall yield, which was subsequently glycosylated to give the target molecule. This flexible route will provide various glycolipids for further exploration of this interesting biological process.
AB - α-Galactosyl ceramide has been identified to be a potent stimulatory agent for a novel immunological process, mediated by CD1 molecules. This paper describes a short and efficient synthesis of α-galactosyl ceramide. Starting from commercially available 2-deoxy galactose, a suitable sphingosine derivative was obtained in nine steps and 36% overall yield, which was subsequently glycosylated to give the target molecule. This flexible route will provide various glycolipids for further exploration of this interesting biological process.
UR - http://www.scopus.com/inward/record.url?scp=0037189212&partnerID=8YFLogxK
U2 - 10.1021/jo0201530
DO - 10.1021/jo0201530
M3 - Article
C2 - 12076157
AN - SCOPUS:0037189212
VL - 67
SP - 4559
EP - 4564
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 13
ER -